[reaction: see text] Follicular fluid-meiosis activating sterol (FF-MAS) has been shown to be an efficient inducer of meiotic maturation. It can potentially be used for improvements of in vitro fertilization techniques. Two short synthesis of FF-MAS are presented in this article. Both syntheses are based on microbiological degradations of sterol side chains. FF-MAS can be synthesized in nine steps from commercially available starting materials by both routes.
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Investigation of FF-MAS oxysterole's role in follicular development and its relation to hedgehog signal pathway.
Sci Rep
October 2024
Faculty of Medicine, Department of Histology and Embryology, Hacettepe University, Ankara, Turkey.
Article Synopsis
- The Hedgehog signaling pathway is important for folliculogenesis, but its relationship with FF-MAS oxysterol in this process, especially in conditions like PCOS, is not well understood.
- *The study found that FF-MAS enhances the proliferation of granulosa cells (GCs) and increases key Hedgehog pathway components (SMO and Gli1) even in the presence of an inhibitor, suggesting its significant role in follicular development.
- *Ultimately, this research could lead to new strategies for improving human IVF treatments by leveraging FF-MAS's effects on GCs and folliculogenesis.
Processive kinetics in the three-step lanosterol 14α-demethylation reaction catalyzed by human cytochrome P450 51A1.
J Biol Chem
July 2023
Department of Biochemistry, Vanderbilt University School of Medicine, Nashville, Tennessee, USA. Electronic address:
Cytochrome P450 (P450, CYP) family 51 enzymes catalyze the 14α-demethylation of sterols, leading to critical products used for membranes and the production of steroids, as well as signaling molecules. In mammals, P450 51 catalyzes the 3-step, 6-electron oxidation of lanosterol to form (4β,5α)-4,4-dimethyl-cholestra-8,14,24-trien-3-ol (FF-MAS). P450 51A1 can also use 24,25-dihydrolanosterol (a natural substrate in the Kandutsch-Russell cholesterol pathway).
View Article and Find Full Text PDFMeiosis-activating sterol synthesis in rat preovulatory follicle: is it involved in resumption of meiosis?
Biol Reprod
December 2004
Bernhard Zondek Hormone Research Laboratory, Department of Biological Regulation, The Weizmann Institute of Science, Rehovot 76100, Israel.
Meiosis-activating sterol (MAS) was shown to overcome the inhibitory effect of hypoxanthine on spontaneous maturation of mouse oocytes and was suggested to mediate the stimulation of meiosis by gonadotropins. Follicular fluid (FF)-MAS is synthesized by cytochrome P450 lanosterol 14alpha-demethylase (LDM). Follicular LDM was preferentially localized in oocytes by immunohistochemistry.
View Article and Find Full Text PDFA functional cytochrome P450 lanosterol 14 alpha-demethylase CYP51 enzyme in the acrosome: transport through the Golgi and synthesis of meiosis-activating sterols.
Endocrinology
March 2004
Laboratory for Medical Genetics, Institute of Biochemistry, Faculty of Medicine, University of Ljubljana, SI-1000 Ljubljana, Slovenia.
Mammalian lanosterol 14 alpha-demethylase (CYP51) is a microsomal cytochrome P450 that demethylates lanosterol to FF-MAS, an oocyte meiosis-activating sterol and late intermediate of cholesterol biosynthesis. Herein we report CYP51 unequivocally localized to acrosomal membranes of male germ cells in mouse, bull, and ram, in which it synthesizes FF-MAS in the presence of the acrosomal form of nicotinamide adenine dinucleotide phosphate reduced-P450 reductase. In the mouse, CYP51 (53 kDa) resides in endoplasmic reticulum (ER) and Golgi during all phases of acrosome development, indicating an intracellular transport from ERs through the Golgi to the acrosome.
View Article and Find Full Text PDFTwo syntheses of FF-MAS.
Org Lett
May 2003
Schering AG, Corporate Research, Research Center Europe, Medicinal Chemistry, D-13342 Berlin, Germany.
[reaction: see text] Follicular fluid-meiosis activating sterol (FF-MAS) has been shown to be an efficient inducer of meiotic maturation. It can potentially be used for improvements of in vitro fertilization techniques. Two short synthesis of FF-MAS are presented in this article.
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